Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(R)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester

Base Information

• Chemical Name: Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(R)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester
• CAS No.: 1053243-31-4
• Molecular Formula: C₅₇H₆₂O₁₁
• Molecular Weight: 923.113

Synonyms:Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(R)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester

Chemical Property of Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(R)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(R)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester

There total 18 articles about Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(R)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

benzyl bromide (100-39-0) → Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(R)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester (1053243-31-4)

Guidance literature:

Multi-step reaction with 12 steps

2: 3-Angstroem molecular sieves, NaHCO₃, Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

3: 0.02percent NiCl₂ in CrCl₂ / tetrahydrofuran; dimethylformamide / 12 h / Ambient temperature

4: 89 percent / H₂ / 10percent Pd-Pb/CaCO₃ / methanol / 12 h / 760 Torr / Ambient temperature

5: 88 percent / NaH, imidazole, (n-Bu)4NI / tetrahydrofuran; dimethylformamide / 1.) room temp., 15 min, 2.) 6 h

6: 91 percent / OsO₄ / tetrahydrofuran; pyridine; toluene / 48 h / -35 °C

7: 1.) Bu₂SnO, 2.) CsF, (n-Bu)4NI / 1.) toluene, reflux, 2 h, 2.) DMF, room temp., 36 h

8: 95 percent / pyridine, 4-(dimethylamino)pyridine / 0.5 h

9: 95 percent / 80percent aq. AcOH / 12 h / Ambient temperature

10: pyridine / 9 h

11: NaH, imidazole / tetrahydrofuran / 0.33 h / 0 °C

12: DDQ / CH₂Cl₂ / 2 h / 0 °C / pH 7 phosphate buffer

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; 3 A molecular sieve; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; Lindlar's catalyst; palladium-lead; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00080a016

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threitol (84379-53-3) → Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(R)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester (1053243-31-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 3-Angstroem molecular sieves, NaHCO₃, Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

2: 0.02percent NiCl₂ in CrCl₂ / tetrahydrofuran; dimethylformamide / 12 h / Ambient temperature

3: 89 percent / H₂ / 10percent Pd-Pb/CaCO₃ / methanol / 12 h / 760 Torr / Ambient temperature

4: 88 percent / NaH, imidazole, (n-Bu)4NI / tetrahydrofuran; dimethylformamide / 1.) room temp., 15 min, 2.) 6 h

5: 91 percent / OsO₄ / tetrahydrofuran; pyridine; toluene / 48 h / -35 °C

6: 1.) Bu₂SnO, 2.) CsF, (n-Bu)4NI / 1.) toluene, reflux, 2 h, 2.) DMF, room temp., 36 h

7: 95 percent / pyridine, 4-(dimethylamino)pyridine / 0.5 h

8: 95 percent / 80percent aq. AcOH / 12 h / Ambient temperature

9: pyridine / 9 h

10: NaH, imidazole / tetrahydrofuran / 0.33 h / 0 °C

11: DDQ / CH₂Cl₂ / 2 h / 0 °C / pH 7 phosphate buffer

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; 3 A molecular sieve; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; Lindlar's catalyst; palladium-lead; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00080a016

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threose (100906-42-1) → Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(R)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester (1053243-31-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 0.02percent NiCl₂ in CrCl₂ / tetrahydrofuran; dimethylformamide / 12 h / Ambient temperature

2: 89 percent / H₂ / 10percent Pd-Pb/CaCO₃ / methanol / 12 h / 760 Torr / Ambient temperature

3: 88 percent / NaH, imidazole, (n-Bu)4NI / tetrahydrofuran; dimethylformamide / 1.) room temp., 15 min, 2.) 6 h

4: 91 percent / OsO₄ / tetrahydrofuran; pyridine; toluene / 48 h / -35 °C

5: 1.) Bu₂SnO, 2.) CsF, (n-Bu)4NI / 1.) toluene, reflux, 2 h, 2.) DMF, room temp., 36 h

6: 95 percent / pyridine, 4-(dimethylamino)pyridine / 0.5 h

7: 95 percent / 80percent aq. AcOH / 12 h / Ambient temperature

8: pyridine / 9 h

9: NaH, imidazole / tetrahydrofuran / 0.33 h / 0 °C

10: DDQ / CH₂Cl₂ / 2 h / 0 °C / pH 7 phosphate buffer

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; acetic acid; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; Lindlar's catalyst; palladium-lead; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00080a016

upstream raw materials:

benzyl bromide

2-O-benzyl-3,4-O-isopropylidene-L-threitol

2-O-benzyl-3,4-O-isopropylidene-L-threose

1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene

Downstream raw materials:

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-hydroxymethyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-yl ester

(2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-dihydro-pyran-3-one

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-yl ester

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 1053243-31-4 Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(R)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester

Send

Send

Metric Ton KG G Pound L ML

Send

Send